One of the facts of owning a car, any car, is insurance. In Ontario, liability insurance is mandatory. Collision and comprehensive coverage is not. Older cars that are keepers rather than beaters should really have specialty coverage (which includes collision and comprehensive) to protect the time and money their owners have invested in them.
Most insurance companies generally focus on newer cars and have problems with older cars, especially those over 20 years of age. They often want appraisals done on them, even though the car is a winter beater and the annual premium costs more than the car is worth.
Whatever policy you have (assuming you're in Ontario), you need to make sure that you at least have either Limitation of Amount Endorsement (OEF 19) or preferably Agreed Value Endorsement (OEF 19A). RoadShow Automotive Appraisals' FAQ does a good job of explaining the difference. For the car owner, endorsement OEF 19A is the one he really should have in his policy. You can find out more about automobile insurance on the Financial Services Commission of Ontario web site.
When you buy insurance, it is important to provide full disclosure of use and nature to the insurance company. For the classic car owner, he might be able to save some money by stating that his vehicle is only for pleasure use even though he drives it regularly to work (misrepresentation). For the hot-rodder, he might be able to save some money by stating that his vehicle has the original 6-cylinder engine even he has replaced it with a high-output V8 engine (material change of risk). The danger is that, upon attempting to make a claim, an investigation by insurance company reveals that the actual use or nature of the vehicle is substantially different than what was originally disclosed. The insurance company could then completely deny coverage without even a refund of the premiums.
Because insurance companies generally don't understand the subtleties of owning an older vehicle, it is best to obtain coverage from an company that specializes in this type of coverage. Many collector car owners in Ontario often obtain their insurance coverage from the following companies:
Auto Insurance Companies on the Internet
For other vehicles, it is wise to check other companies for their rates. Besides looking for the lowest rates, it is also wise to check the experience of others. Sometimes the lowest rate isn't the cheapest if they don't give you good service when you need help.
Many companies world-wide offer insurance quotes over the internet and it pays to shop around.